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Oluwasegun Adegboye has been working since 2011 when they began their graduate studies at the University of Ilorin. In 2014, they completed an internship at Tuyil Pharmaceutical Industries Limited. In 2016, they volunteered at Kids & Teens Resource Centre and worked as an Administrative Assistant at Ikpoba Okha Local Government Secretariat (Primary Health Care Unit). In 2017, they worked as an Energy Officer at Greenlight Planet, Inc., and as a Mobilizer (contract staff) at Catholic Relief Services. Oluwasegun also served as the President (Idogbo C.D.S Zone) of the National Youth Service Corps. In 2018, they were a Business Development Executive at Pagatech Limited and a Marketer at Access Bank Plc. In 2022, they began working as a Regional Sales Manager at OurPass (Techstars '21).

Oluwasegun Adegboye's education history includes a Bachelor of Science in Microbiology, General from the University of Ilorin, obtained in September 2016. Prior to that, they obtained a SSCE from Oyeleke Memorial College, Offa in 2010. Oluwasegun also holds several certifications, including VLookup and Functions from dbrownconsulting in October 2020, a Certificate of National Service from the National Youth Service Corps in October 2017, a Certificate of Participation from NYSC/NDLEA Drug Free Club, Edo State from the National Youth Service Corps in January 2017, Autocad Engineering from EVA GREEN, Abuja in July 2011, a Certificate in IT Excite from NIIT Technologies Limited in November 2010, a Base Certificate in Microsoft Access from NIIT Technologies Limited in September 2010, a Certificate in Citizenship and Leadership Training from the Federal Ministry of Youth Development, Nigeria in April 2009, and a Certificate of Participation in an Intensive Training on the Production of Soap, Insecticide, Hair Cream, Pomade, Juice and Dye from Philips Chemical Engineering Consultant in 2009.